


Dean Winchester’s Guide to Successfully Hacking a Date

by chucks_prophet



Category: Supernatural
Genre: Castiel is a Sweetheart, First Dates, Fluff, Fluff and Humor, Hacker Charlie, Hacker Dean, Light Angst, M/M, Rated for Lots of Sexual Innuendos I dunno what happened there whoops, References to Canon, Rich Castiel, Working a Job
Language: English
Status: Completed
Published: 2017-05-21
Updated: 2017-05-21
Packaged: 2018-11-03 03:59:51
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,187
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10959195
Author URL: https://archiveofourown.org/users/chucks_prophet/pseuds/chucks_prophet
Summary: “Holy shit.”“He comes from a family of crooks, Dean.”“Yeah, a  handsome  family of crooks.”





	Dean Winchester’s Guide to Successfully Hacking a Date

**Author's Note:**

  * Inspired by [Reunion](https://archiveofourown.org/works/10918113) by [Shannon-Kind (Shannon_Kind)](https://archiveofourown.org/users/Shannon_Kind/pseuds/Shannon-Kind). 



 

“Holy shit.”

“He comes from a family of _crooks,_ Dean.”

“Yeah, a _handsome_ family of crooks.”

“No. No!” Charlie argues. “Whatever morally inappropriate thing you’re thinking about doing, you can stop thinking about it right now.”

“Is that it, _Mom?_ ” smarts Dean. “Charlie, we’re _hackers._ What morality do we have?”

Charlie scoffs, her hair like her words: fiery as she stalks off with both of them. It’s not a fair fight with Dean, who tends to be… stubborn about certain things. His father used to call him the horns to his oxen. John was big and tall—one look from him sends anyone within a five mile radius scrambling for the hills, but Dean can be nastier when he wants something really bad.

But Dean’s mellowed out since, deciding to retire from bounty hunting to a nice, quiet life as a hacker (minus the few times the police were able to track his IP address, of course, but he’s used to moving around with an ex-Marine father)—taking down the bigger guy with his fingers rather than his whole hand. And sure, it’s not the apple pie life, but Dean gave up on that _Better Homes and Gardens_ fantasy long ago. Let’s just say his stubbornness took a toll on the two people he cared about most.

Dean only knows him from the profile Charlie pulled up. Castiel James Novak. Dark brown hair that defies the rules of sex by screaming “post-coitus”. Blue eyes. Large, chapped lips and a smile that could melt the unopened bag of M&M’s next to Dean. Jawline like a table littered with fallen pepper—barely-there stubble extending well into his neck, which his plenty kissed by the sun, but not by human lips, which is absolutely baffling. 29. Scorpio. Sexually expressive, especially with an Aquarius... which Dean just so happens to be.

Not that Dean reads horoscope compatibilities.

Anyway, _and_ he’s the founder of Angel Wings—a non-profit organization that takes in homeless youth and gives them resources to reconnect them with society.

And Charlie set him up on a-a blind hack date with this guy?

Dean’s not a devout man, but Jesus Christ, he’s screwed. Why does he have to have such a long password? Why can’t he be like everyone else and have it be his high school football team and his graduation year?

“Charlie’s right, you know,” Ash chimes in from behind Dean, “He’s just another rich shmuck who wants to feel good about himself. Meanwhile, did you hear about the oil spill in the Atlantic? Not one penny was donated to the recovery fund. Now _that’s_ some screwed up shit.”

“We steal money too, you know,” Dean argues.

“Yeah, but we don’t steal it from the helpless.”

Dean turns around in his ratty old chair with a scoff, “You can wipe the taste of the boss’s ass from your lips.”

“Hey, Frank may be a little bonkers, but at least he’s careful.”

“Careful and paranoid are two different ballgames.”

“Either way, you better grease up your bat, Don Juan, because you’re playing ball,” Ash says, groaning as he stands up and starts to stretch behind that cramped little workspace of his. It has to be littered with at least ten takeout bags that act as a fort around his laptop, which is always in tip-top shape. No dust, no scratches—not even a single strand of that long, mullet-rock hair of his tucked between the keys. Dean’s checked.

Dean cocks his head, trying to wrap it around that analogy as Ash pats him on the shoulder in passing. “Wait! Is the bat a metaphor for… oooh.”

***

It’s just a few questions.

All Dean has to ask are a few security questions disguised as getting-to-know-you questions and he can enjoy himself however he wants the rest of the night.

The greeter spots Dean walking in and jumps to guide Dean into the restaurant, “Right this way, sir. Mr. Novak is going to be in the table closest to the window. And might I say, he looks ravishing.”

_Ravishing._

Dean scoffs. What has the team gotten him into this time?

When the two of them approach Castiel, of course—of _course—_ he’s wearing a three-piece suit with a blue tie that conveniently brings out his eyes over a white blouse that’s unbuttoned enough to expose a little bit of his chest. He’s not sure what the beige trenchcoat over the black blazer is about, but Dean’s more concerned with what’s _underneath_ all of that, because wow.

Dean hates to say he feels separation anxiety from the greeter when he leaves, but it’s only because he leaves him with the man in front of him, whose lips are curving into a crooked smile at the sight of Dean in all his glory: In a blazer and a faded Soundgarden tee and black jeans. He even parted his hair for the occasion. He wasn’t planning on doing that until his little brother’s wedding.

“Dean Paul Bonham?” he inquires, and _okay,_ that’s a hell of a raspy voice.

Dean huffs a laugh. The aliases just keep getting better and better. He guesses it could be worse, Charlie could’ve spited him by changing his last name to Bieber or Timberlake. “You can just call me Dean,” he says, accepting the hand that’s offered to him as Castiel steps out of his chair to personally shake his. “Nice to meet you, Castiel.”

“ _Aww, you’re on a first-name basis already. GAG!”_

Dean refrains from rolling his eyes. He nearly forgets about the earpiece when Castiel starts to pull out Dean’s chair for him. Having Charlie in his ear all night is going to be a nice third wheel he didn’t ask for.

“Likewise,” Castiel says as he takes his seat again. “Please, call me Cas. I love my mother, but I’d only like to see her a couple times a week.”

Dean blushes, and replies with a simple, “Alright.” There’s a silence that passes between them, because Dean can’t stop staring and thinking about taking a to-go back for the meal in front of him. But Charlie won’t let him have it: “ _Perfect lead-in. Ask him about his mother’s maiden name. Play it off like a joke or something.”_

Dean clears his throat, “So, um… do you call your mother by her full name, too?”

“No, no,” Cas laughs, “I don’t think she would appreciate that very much. Her maiden name, Shurley, reminds her too much of Shirley Temple, which was coincidentally her nickname and basically the bane of her existence growing up. It didn’t help that she had strawberry blonde hair.”

“ _No hits.”_

“Wait. Shurley?” Dean asks. “Is she related to Chuck Shurley?”

Cas smiles shyly. “Yeah, actually. Chuck’s my uncle.”

“You’re serious?” Dean scoffs, leaning over the table to emphasize his genuine excitement, “I _love_ the Supernatural books! I follow him on every social media platform—I… sorry.”

_“I’ll look into that. Chuck Shurley. Or better yet, just tell me where he lives, Dean.”_

Cas bites back a laugh, “You’re sure? I could call him up right now.”

Dean picks his jaw up from off the table and blinks a few times. “No—no, it’s okay.”

_“Oh yeah, show him the pentagram tattoo just below your collarbone. I’m sure he’d love that. Or, better yet, let him put out the flames with his—”_

Dean slaps his ear with his palm—hard, too—much to the surprise of the people around them and Cas.

“Uh, everything okay?” Cas asks, obviously containing himself to a mild concern.

Dean scratches the back of his neck. “Yeah. It was just a fly.”

“Oh. You must be _extra_ sweet, then,” Cas says with a wink as their waiter approaches their table. Cas, to Dean’s surprise, orders a burger and a glass of wine.

Dean orders the same and makes that a _double_ glass of wine.

*

“ _He has a hamster named Clarence? Dean-o, what did we get you into? Oh well, I’ll try that…”_

“Ten, actually,” Cas clarifies. Dean’s eyes widen as he hears the faint typing of Charlie’s keyboard stop with an exasperated sigh. “What? The pet shop was closing down.”

Dean chuckles, “No, it’s not—um… my brother has seven dogs. And not like Chihuahuas or Terriers, full-grown dogs. Retrievers, Shepherds, Pinschers… _and_ he and his fiancée are expecting.”

“Wow,” Cas breathes through a laugh of his own, “I salute him on not having a full-blown allergy attack.”

Dean cocks his head, nodding. “Yeah. He hasn’t had the same energy since.”

“I can imagine, chasing after all those dogs. And with a child on the way.”

“Oh no, because of all the Benadryl he takes.”

Cas laughs, but it’s brief this time. Before Dean can question, Cas says, “I know with a name like mine, you probably associate me with the oil spill a few weeks ago.”

Dean’s mouth parts. “Cas, I—I wasn’t—”

“It’s okay, Dean, really,” Cas says, forcing a small smile. “I can’t excuse my family’s actions. But you have to believe me when I say that I did everything in my power. I got my team at Angel Wings together to go out and help clean the affected animals. I couldn’t stand to see them in that condition, but we managed to save a lot of them. We even paid for the medical attention of a few of the crew members that were on duty that day—anonymously, of course, because they wanted nothing to do with the Novaks after they found out their workman’s comp wouldn’t cover their bills.”

Charlie’s thoughts on the other end sum up his perfectly: “ _Oh shit.”_

“Why didn’t I hear about that in the news?” Dean asks after their waiter brings their check. “That could’ve been good exposure for your family.”

“Nothing good comes out of the news,” Cas says. “And even if it had, I didn’t care about the publicity. Or my family’s reputation. I just wanted to help reverse the damage in any small way I could.”

Dean sighs, and apparently, that’s all it takes for Charlie to say: _“Dean. Don’t do it. We can’t risk it.”_

But damn the risk. Cas is a handsome, funny, charming, kind, and selfless human being.

And Dean is still a stubborn son of a bitch.

“My name’s not really Dean Paul Bonham,” he says, “it’s Dean Winchester. And no, it’s not a coincidence that you matched with me on your dating profile. I mean, we both like burgers, but aside from that—”

“Dean—”

“I’m a hacker,” Dean continues, “It’s what I do. The plan was to get to know you on a deeper level so that we could eventually tap into your family’s personal funds and… reprioritize… a little bit—”

“Dean, I know.”

Dean’s breath catches in his throat. “I… what? How?”

“The slap you gave to your ear earlier,” Cas laughs, “you aren’t exactly discreet.”

“I’m more confident behind a screen,” Dean admits, heart still thudding in his chest. “But… you’re not mad?”

Cas shakes his head with a smile, “You’re not the first person who’s tried to take me down. It’s usually not this elaborate, but. And I probably deserve it. I used to work for family, and I saw all the unjust things they were doing—all of it. But I couldn’t bring myself to speak up about it, so I quit when I was shy of seventeen. Started a non-profit for kids like me, no home, no purpose.”

Cas draws his bottom lip between his teeth as he looks up at Dean again. “I regret a lot of things, Dean. But this date wasn’t one of them. _You_ aren’t one of them. You’re just doing your job, like I was—like I _should’ve.”_

Dean’s lips twitch into a smile. It’s been a while since someone’s shown interest in him. He forgot how it felt, the feeling like he’s floating from all the butterflies in his system. “For the record,” he says, “I’m officially off the clock.”

Cas laughs, “Good to know. Where did Paul Bonham come from, by the way?”

“Oh, Paul is from John Paul Jones, the instrumentalist for Led Zeppelin, and Bonham as in John Bonham, the drummer for the same band.”

“Led Zeppelin,” Cas says, considering. “I’m not sure if I’ve heard their music.”

“Seriously?” Dean scoffs, bringing his finger to his chin in mock-thought. “I… no. No, that’s not acceptable. I might have a tape in my car for you to borrow in the meantime.”

“In the meantime?”

“While I make you a mixtape,” Dean says, then stops, realizing: “I mean, if that’s not too weird.”

Cas smiles with all his teeth, and Dean might just be rethinking the apple pie life with the white picket fence, “No. Not at all. We’re heading to your car anyway, right?”

Dean cocks his head at the inquiry, but gets the hint when Cas gets up and purposely leans into Dean’s ear with the earpiece to whisper something hot and fleeting.

_“Oooookay, yeah, no, I’m signing off before I hear anything else that’ll give me waking nightmares until I’m 40. Have fun, Dean-o.”_

**Author's Note:**

> The Soundgarden reference was for the late Chris Cornell. What a talent. R.I.P., good sir.


End file.
